Ethyl orthopropionate → 4-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 44751

Reaktionsgleichung

Reaktionsgleichung von HRID 44751
C(O[C:4](OCC)(OCC)[CH2:5][CH3:6])C.Cl.N1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:30]=1[NH:31][CH2:32][C:33]1([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[CH:28][CH:27]=[CH:26][CH:25]=2>C1(C)C=CC=CC=1>[CH2:5]([C:6]1[N:31]([CH2:32][C:33]2([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:20]=1)[CH3:4]

Komponenten

5

Edukt 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 574578244-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol

Produkt 1

HCID 575154484-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Triethylorthopropionate (2.4 mL, 12.0 mmol) and pyridine hydrochloride (60 mg, 0.5 mmol) were added to a suspension of 4-[(3-aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux for 2.5 hours and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the filtered to provide 4-[(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. filtrationthe filtered

Quellen und Nachweise

ORD-Eintrag
ord-dd84ae6a85114035b160151e3033b8fc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

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